AnnE Diemer

Introduction

Hiring is one of the highest impact things you can do for your company at any stage, but particularly in the early stages. Bringing new people on board will accelerate your work output, expand your company’s capabilities, and bring new skills, expertise, experiences, and perspectives to the work your company does. Your early team sets the foundation for your company’s culture.

The first place that founders should look for new team members is their close network—people whose work they are already familiar with, people they know they can partner with during the ups-and-downs of early-company life. These people are more likely to take a bet on you and your idea.

However, that pool of people is likely very small and they may not have the many, many competencies required to run a business. This guide will help you find great new team members beyond that first set of people.

Step 1: Determine what roles you want to hire for and their core responsibilities

The first thing to think about is what qualities will improve the team. When a company is starting out, there is a temptation to reproduce what’s working well. But you want to complement your team, not duplicate it.

A good place to start is by making a list, in very concrete terms, of what the team is struggling with and what skills and expertise the business is currently blocked on. This list should include both hard skills (e.g. infrastructure engineering, operations, frontend design, sales, marketing) and soft skills (e.g. communication, organization, relationship building, influencing).

Then, pick out which skills on that list could likely fit together within a single person’s responsibilities at your company (for example, it’s likely that sales, operations, and relationship building skills could fall under one role). As you do this, document what backgrounds and experiences would make someone an attractive candidate to do this role at your company. Do you want someone with B2B sales experience at a company of a similar size? Do you want someone who has built a security program from scratch before? As you create this list, it’s important to have a reason for each thing you add–—everything should be directly applicable to the work the person will be doing at your company.

This is the start of a job description. To test if you’re designing a reasonable role, write down what a typical day or quarter would look like for a person in this job. If someone executed perfectly in this day or quarter you designed, would it meaningfully and reliably drive impact for the company and business? Will executing at that level even be feasible and fulfilling for a single person?

If the answer to both questions is “yes”, then it’s time to create and post a formal job description.

Step 2: Post a role with a clear, motivating job description on your website

Writing out exactly what you are looking for will set explicit expectations with candidates about what is needed of them to be successful. This will ensure that you and your candidates have a great experience determining whether there is a mutual fit. It will also help you more easily spread the word.

The best job descriptions follow a simple formula: (a) a description of the company, (b) an explanation of the role, and (c) the criteria you’re seeking in a candidate. Fortunately you wrote parts (b) and (c) in step 1.

When you post your job description, make sure to use clear, inspiring, and inclusive language. (It can be hard to determine if you’re unintentionally using exclusionary language. Textio has some great tips for writing inclusive job descriptions.) A potential candidate should have a very good sense of the company, team, and role from reading the job description. Including extraneous or exaggerated information could prevent qualified candidates from applying and could set the wrong expectations with people who do apply.

Step 3: Fill your pipeline with excellent candidates

Once you post your job description, there are a number of ways to find candidates. Four that work particularly well are sourcing sessions, LinkedIn, in person events, and third-party job sites.

Host sourcing sessions

A “sourcing session” is time explicitly carved out to write down people in your network, and on the periphery of your network, that may be a good fit for a role at your company. Sourcing is easy to deprioritize, but it’s absolutely critical to building a sizeable and diverse pipeline. At Stripe, our sourcing sessions are one hour long, and we invite everyone from relevant teams to fill out a spreadsheet with people we’d love to hire.

Tips for an effective sourcing session:

Start with the context and motivation for hiring for the role. This will get everyone on the same page about the role and hopefully inspire people to help.

Set a clear individual or team goal. For example, everyone finds 10 candidates or the group finds 50 candidates in aggregate.

Provide a central resource (e.g. a spreadsheet) for keeping track of candidates. This will not only help you stay organized later with your outreach, but it can also be a source of motivation for people attending the sourcing session.

Have someone available who can answer questions about the role and its qualifications.

Bring music and snacks! Who doesn’t like music and snacks?!

Take the entire hour—no matter what. People always remember the perfect candidate ten minutes after they’ve gone through their entire network.

Encourage participants to show each other candidates they’re thinking about.

Encourage participants to share destinations where they’ve had success sourcing. For example, GitHub, LinkedIn, or AngelList.

List potential candidates even if you know they’re not looking for a new role. Even if a potential candidate doesn’t want to join now, she may in the future or she may know people who are looking now.

Remind the group to dedicate extra time and energy looking for candidates from potentially atypical or underrepresented backgrounds.

Use LinkedIn

If you use just one tool for recruiting and sourcing, use LinkedIn. LinkedIn is the best starting place for sourcing.

The key to using LinkedIn effectively is translating your role criteria to your LinkedIn search. Some specific tips:

Use keywords to identify candidates with relevant job titles and descriptions of what they are working on. In general, more specificity is better.

Find additional keywords by asking yourself why you’re searching from particular sources. “I’m looking for someone from Facebook.” “Why?” “They are familiar with working with large user bases.” “Oh, I should think about large user bases in general, not just Facebook.”

Use “years of experience”, “years in current role”, or “years since graduation” to determine tenure.

When you find a profile that is a fit, read through it thoroughly to see what keywords it includes. Then search for those keywords. You may find candidates you wouldn’t have found otherwise.

Target companies, groups, and schools with demographics you want to emulate. When you hire from a particular source, you lay the foundation to inherit their successes and challenges with diversity.

If you recruit often, consider getting LinkedIn Recruiter. It will enable you to perform more targeted searches and reach out to a larger pool of candidates than you’d otherwise be able to.

Attend events

Events are one of the best ways to prospect candidates. You may already have a list of industry events and conferences that you regularly attend. If so, continue to go to those if you find them valuable. Eventbrite and Meetup are great platforms to help you identify unique events that may not be on your radar. Need to recruit someone for the hardware team? Go to a Makerspaces meetup. Need a copy editor? Maybe there are National Novel Writing Month meetups in your area.

The key is to go to events that you’re actually excited to go to. You’ll show up with real, genuine excitement, and it’ll be easier to find candidates with a shared interest.

Once you’ve picked a few events, here are some tips for attending:

Set a goal. Before arriving at the event, decide how many people you want to talk to. If there’s a guest list available ahead of time, do your research and seek out high-potential candidates.

Be yourself. Authenticity is critical for all interactions with potential candidates, and especially for in-person interactions. You don’t have to be talking about your company or hiring at every turn. Real, genuine networking is part of recruiting.

Prepare your company/role pitch. Make sure you are prepared with a succinct and memorable explanation of your company and the roles you are looking to hire for. Be prepared to answer “What do you do?” or “What does your company do?” Even if you’re talking to someone who is uninterested in joining, your pitch should be clear enough that they can tell their friends about open roles in your company.

Tailor your pitch to your audience. When I talk about Stripe at non-profit events, I talk about Stripe Atlas and building opportunities for entrepreneurs all over the world. But when I’m at a VC event, I talk about the potential of Stripe’s products to provide more tools than other companies who are also in the FinTech space.

Post on third-party job sites

Some people haven’t visited your company’s jobs page because they haven’t heard of your company yet. This is why third-party job sites like Craigslist, AngelList, or Handshake can be so effective.

To identify which would be best for you, ask others in your industry where they’re having success. You should also ask candidates where they’re searching for jobs.

When evaluating third-party sites, don’t be afraid to reach out to the company that runs the job board to ask them questions. What is their rate of hire? What type of people visit their site?

Another thing to consider is that some job boards require payment. You’ll need to determine whether their traffic and audience is worth the cost. If you can, implement a unique tracking link for each job site so that you can learn about and optimize your sourcing activity.

There are enough job boards out there that you can be very discerning and targeted. Platforms like Hacker News and Hired are really effective for finding engineers. There are also a handful of job sites that are focused on highlighting candidates from underrepresented backgrounds like Tech Ladies and jopwell.

Step 4: Talk to candidates in a way that gets them excited

Once your list of candidates is in place, there are two types of outreach:

Warm outreach. This is outreach to people you know. Warm outreach should be personal and colloquial to keep the barrier to responding low. Talk about your experience at the company and how it relates to something she is great at and/or passionate about.

Cold outreach. This is outreach to people you don’t know. Cold outreach should be short, sweet, and personalized enough to express your excitement about talking to this specific candidate. Think about what would catch your eye, and then write that to maximize your chance of a response.

Both types of outreach can be intimidating for their own reasons, but they are each critical to getting the word out that you’re hiring. You always want to make the outreach as pleasant and personal as possible while including critical information about the role.

Warm outreach

When doing “warm outreach”, it’s most effective to either (1) have the person with the closest relationship reach out first or (2) have a senior team member reach out and mention the close connection (“AnnE said you’re the best engineer she’s ever worked with!”).

Here are some examples of warm outreach you can customize and make your own.

Hi Lauren! Hope you’ve recovered from dinner on Monday! I’m writing you because my team just opened a role and as soon as I read the description, I thought of you. We need someone who can help get our recruiting processes in order and running smoothly, and someone who understands how to work cross-functionally with our People Ops team to help build a smooth hire-to-onboarding process. I know you’ve rolled something like this out at your company—any interest in learning more about the role here? Obviously, I’m happy to talk to you about it, but also, would love to set you up to talk to the Head of Recruiting! (I showed her your profile and she said she’d talk to you today if you wanted to!) Let me know :-)

Hi Rachel! I’m excited to see you at WriterCon next week. Quick question—we’re looking for our next content editor at Stripe and I wanted to see if you or anyone you know would be interested? This role is going to be key for Stripe so we really want to find the right person. I know you’re super happy where you are, so no pressure, but would love to talk to anyone you think is great. You’d know best!

Hi Cait! My name is AnnE, and I graduated from Howard in 2015. I’m reaching out because my team is hiring software engineers at Stripe and I think the team could use some more Howard grads! The people here are amazing—there are so many opportunities to learn. And on top of that, the salads at lunch seriously rival the ones from our Hall ;-) I’d love to have you come to the office for lunch if you’re interested?

If someone writes you back but isn’t interested, ask them if they know anyone who is.

Cold outreach

When doing cold outreach, be concise and welcoming. Speak to something that they care about and let the potential candidate know why you are reaching out to her, specifically. Rather than trying to schedule an interview or asking her to come to the office, make the ask easy to respond to by offering to share more information or have a quick phone call.

Here are some examples of cold outreach you can customize and make your own:

Hi Jaime! I lead the Editorial team here at Stripe. I’m reaching out because I was really impressed by your work on the blog. I’d love to talk to you more about it. Any interest in meeting up for coffee?

Hi Alba! I’m working on the Editorial team at Stripe. I noticed that your work on your company’s blog looks like a great fit for some of the material we are creating here. Right now, my team is working on making the blog the go-to destination for scaling organizations. I’d love to jump on a call with you to tell you more about it and see if this is something you’d be interested in working on in the future.

Hi Jesse! I’m working on hiring a fantastic writer at Stripe. Historically, we’ve empowered entrepreneurs with our products and infrastructure and increasingly we want to do it with information too! I came across your profile and was impressed by your experience—I’m sure you’re not looking to move jobs at this time (congrats on two years at Slack by the way!), but I would love to hop on a call for five minutes to talk about this role and get any suggestions you have for finding someone with similar experience? Thanks so much in advance!

Two more tips for cold outreach:

Follow up. Always, always follow up. Candidates who don’t respond to your first message may very well respond to your second or third note. It shows that you are interested and persistent. I know from experience that this can feel like you’re pestering disinterested potential candidates (or turning them off!), but you can write in a way that is respectful and earnest by crafting messages that are are short and authentic. (“Hi Jaden, I hope you’re doing well! I’m reaching out to bring my note back up in your inbox. I’d really like to chat with you about the product manager role at Stripe. Are you interested at all? Or, perhaps know anyone who is? Absolutely no worries if not!”)

Stay organized. Do your best to track your candidate outreach and communication using a central tracker for your company (using a spreadsheet or, as you scale, an Applicant Tracking System). This will not only help you keep track of each candidate, but it will also minimize the chance that multiple people at your company reach out to the same candidate.

Step 5: Keep it up

To maintain a steady pipeline, your recruiting efforts need to be a consistent priority. Starting this process early will also ensure that you set up optimal practices as you grow.

The amount of time you devote to recruiting is up to you. At Stripe, we encourage our hiring managers to spend some time every day on recruiting. Some hiring managers prioritize up to two hours a day on building their pipeline, particularly when they are actively hiring. However, even when you aren’t actively hiring, I would recommend taking 20-30 minutes every day to reach out to candidates and build your network. Set this as an event in your calendar and treat it as you would any other priority so that it becomes a habit.

You may not see the effects of all of your work immediately. That’s normal. It takes time to build a pipeline. Even when roles aren’t open or candidates aren’t immediately interested, continue to reach out.

Sometimes this may feel like a waste of time. It’s not. In a few years, when you’re looking back at your company’s accomplishments, you won’t regret the time you spent finding the people that made it possible.

Conclusion

When you start recruiting, looking within your personal network is an easy and obvious starting point, but you shouldn’t limit yourself to that specific group. It’s never too soon to begin recruiting outside of your personal network and start building a more diverse pipeline of candidates. It’s not always a straightforward process—we’re still learning how to do it well—but it is worth the commitment. I wish you the best of luck.